Why does the Torah prohibit in the strongest terms dressing in clothes normally associated with the opposite sex?

The source for this proscription is Deuteronomy 22:5. “No male article (of clothing) is to be worn by a woman, nor may a man wear a woman’s garment. All who do these things are to’eiva (morally repugnant) before G‑D.”

To’eiva is one of the strongest adjectives of disapproval used in the Torah. The Talmud (Nazir 59a) registers surprise. “Surely not to’eiva!” it exclaims in relation to this prohibition. Its answer: in itself maybe not, but the Torah is concerned with outcome. If a man wears women’s clothing, he will come to sit among women and vice-versa.

The Talmud rather coyly leaves it........

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